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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 07:19:57 UTC
Update Date2021-09-26 23:01:44 UTC
HMDB IDHMDB0250327
Secondary Accession NumbersNone
Metabolite Identification
Common NameClioquinol
DescriptionClioquinol, also known as entero vioform or chloroiodoquin, belongs to the class of organic compounds known as chloroquinolines. Chloroquinolines are compounds containing a quinoline moiety, which carries one or more chlorine atoms. Clioquinol is a drug which is used as a topical antifungal treatment. Based on a literature review a significant number of articles have been published on Clioquinol. This compound has been identified in human blood as reported by (PMID: 31557052 ). Clioquinol is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Clioquinol is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.
Structure
Thumb
Synonyms
ValueSource
5-Chlor-7-jod-8-hydroxy-chinolinChEBI
5-Chloro-7-iodo-8-hydroxyquinolineChEBI
5-Chloro-7-iodo-8-quinolinolChEBI
5-Chloro-8-hydroxy-7-iodoquinolineChEBI
7-Iodo-5-chloro-8-hydroxyquinolineChEBI
7-Iodo-5-chloroxineChEBI
ChloroiodoquinChEBI
ClioquinolumChEBI
IodochlorhydroxyquinolineChEBI
IodochlorohydroxyquinChEBI
IodochloroxyquinolineChEBI
5 Chloro 7 iodo 8 quinolinolMeSH
ChinoformMeSH
ChloroiodoquineMeSH
Entero septolMeSH
Entero vioformMeSH
Entero-septolMeSH
Entero-vioformMeSH
EnteroSeptolMeSH
EnteroVioformMeSH
EnteroquinolMeSH
IodochlorhydroxyquinMeSH
VioformMeSH
Chemical FormulaC9H5ClINO
Average Molecular Weight305.5
Monoisotopic Molecular Weight304.910434914
IUPAC Name5-chloro-7-iodoquinolin-8-ol
Traditional Nameclioquinol
CAS Registry NumberNot Available
SMILES
OC1=C(I)C=C(Cl)C2=C1N=CC=C2
InChI Identifier
InChI=1S/C9H5ClINO/c10-6-4-7(11)9(13)8-5(6)2-1-3-12-8/h1-4,13H
InChI KeyQCDFBFJGMNKBDO-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as chloroquinolines. Chloroquinolines are compounds containing a quinoline moiety, which carries one or more chlorine atoms.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassQuinolines and derivatives
Sub ClassHaloquinolines
Direct ParentChloroquinolines
Alternative Parents
Substituents
  • Chloroquinoline
  • 8-hydroxyquinoline
  • 2-iodophenol
  • Aryl chloride
  • Aryl halide
  • Aryl iodide
  • Pyridine
  • Benzenoid
  • Heteroaromatic compound
  • Azacycle
  • Organooxygen compound
  • Organonitrogen compound
  • Organoiodide
  • Organochloride
  • Organohalogen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP3.66ALOGPS
logP3.36ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)7.34ChemAxon
pKa (Strongest Basic)3.28ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area33.12 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity60.13 m³·mol⁻¹ChemAxon
Polarizability22.63 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+149.32430932474
DeepCCS[M-H]-146.52730932474
DeepCCS[M-2H]-182.99830932474
DeepCCS[M+Na]+158.60730932474
AllCCS[M+H]+158.932859911
AllCCS[M+H-H2O]+155.032859911
AllCCS[M+NH4]+162.532859911
AllCCS[M+Na]+163.532859911
AllCCS[M-H]-140.332859911
AllCCS[M+Na-2H]-141.032859911
AllCCS[M+HCOO]-141.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
ClioquinolOC1=C(I)C=C(Cl)C2=C1N=CC=C22666.8Standard polar33892256
ClioquinolOC1=C(I)C=C(Cl)C2=C1N=CC=C21914.3Standard non polar33892256
ClioquinolOC1=C(I)C=C(Cl)C2=C1N=CC=C21923.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Clioquinol GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ufr-2279000000-6cf0bdc100cf284a8ce02021-09-23Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Clioquinol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Clioquinol GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Clioquinol GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Clioquinol LC-ESI-qTof , Positive-QTOFsplash10-0ab9-4931100000-28d4a47f77706f4122132017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Clioquinol , positive-QTOFsplash10-0udi-2901000000-22ecce16d52e911c9ef02017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Clioquinol 10V, Positive-QTOFsplash10-0a4i-0009000000-892c7c5731408fbcc7992016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Clioquinol 20V, Positive-QTOFsplash10-0a4i-0009000000-f8fbc9c4d6bbacbe91f92016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Clioquinol 40V, Positive-QTOFsplash10-0a6r-2089000000-8aabd74206b87576ca6e2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Clioquinol 10V, Negative-QTOFsplash10-0udi-0009000000-03cd6c1f1cfd97367fe52016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Clioquinol 20V, Negative-QTOFsplash10-0udi-0009000000-03cd6c1f1cfd97367fe52016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Clioquinol 40V, Negative-QTOFsplash10-0ufr-4229000000-d5b666aba90b83aef86e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Clioquinol 10V, Positive-QTOFsplash10-0a4i-0009000000-232031ac93f8eb591f402021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Clioquinol 20V, Positive-QTOFsplash10-0a4i-0009000000-232031ac93f8eb591f402021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Clioquinol 40V, Positive-QTOFsplash10-0fb9-0292000000-09fcf691ca3683ac33bb2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Clioquinol 10V, Negative-QTOFsplash10-0udi-0009000000-08a7a28f0c28f4bd6f5a2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Clioquinol 20V, Negative-QTOFsplash10-0udi-0009000000-08a7a28f0c28f4bd6f5a2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Clioquinol 40V, Negative-QTOFsplash10-004i-3093000000-9d35d1f1c3845a4a56b42021-10-12Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB04815
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID2686
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkClioquinol
METLIN IDNot Available
PubChem Compound2788
PDB IDNot Available
ChEBI ID74460
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]